Kristine and Dave became acquainted through the relationship of Kristine's friend, Briann, and Dave's cousin, Brett, where they were Maid of Honor and Best Man at their wedding! While they knew each other for a while, a Labor Day Weekend in Chicago sparked all of this in motion. While at a party, they bonded over Kristine teaching Dave how to make craft cocktails. After they got back home, they kept the conversation going and lead to them into a relationship later that fall.

While on a summer vacation in Chicago, Dave asked if Kristine could "reserve a day" for a few activities. They started the day with lunch at the Russian Tea Time Restaurant for High Tea, followed by a quick stop by the Fine Arts Building right around the corner. They crossed Michigan Ave to stop by the Art Institute, which was somewhat undermined due to the presence of everything a NASCAR race entails. They next sped off to the Adler Planetarium for a star show. On a walk along the Lakefront Trail, Dave popped the question. Each location was to symbolize a certain element of what Kristine means to him and how he wished to spend the rest of his life with her. They ended the day with dinner downtown, to toast their engagement and celebrate together. At last, they came home to a surprise celebration with Dave's parents and Brett and Briann.